Sulfurized estolides and methods of making and using the same

Abstract

Provided herein are compounds of the formula: in which n is an integer equal to or greater than 1; m is an integer equal to or greater than 1; R 2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R 1 , R 3 , and R 4 , independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein at least one of R 1 , R 2 , R 3 , or R 4 is sulfurized or epoxidized. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.

The invention claimed is: 
     
       1. At least one compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein 
         W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , and W 7 , independently for each occurrence, are selected from —CH 2 —, —CH═CH—, —CHR 5 —, and 
       
       
         
           
           
               
               
           
         
       
       provided that at least one of W 1 , W 2 , W 3 , W 4 , W 5 , W 6 , or W 7  is —CHR 5 — or 
       
         
           
           
               
               
           
         
         R 5  is selected from —S v R 6 , wherein v is an integer selected from 1 to 8 and R 6  is selected from hydrogen and an estolide residue; 
         T is S; 
         z is an integer selected from 0 to 15; 
         p is an integer selected from 0 to 15; 
         q is an integer selected from 0 to 15; 
         x is, independently for each occurrence, an integer selected from 0 to 20; 
         y is, independently for each occurrence, an integer selected from 0 to 20; 
         n is equal to or greater than 0; and 
         R 2  is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, 
         wherein each fatty acid chain residue of said at least one compound is independently optionally substituted. 
       
     
     
       2. The at least one compound according to  claim 1 , wherein at least one of
 W 1 , W 2 , or W 3  is —CHR 5 — or 
 
       
         
           
           
               
               
           
         
       
     
     
       3. The at least one compound according to  claim 1 , wherein W 3  is —CH 2 —. 
     
     
       4. The at least one compound according to  claim 1 , wherein W 1  is —CH 2 —. 
     
     
       5. The at least one compound according to  claim 1 , wherein W 2  is selected from —CHR 5 — and 
       
         
           
           
               
               
           
         
       
     
     
       6. The at least one compound according to  claim 5 , wherein W 2  is selected from —CHR 5 —, and R 5  is selected from —S v R 6 . 
     
     
       7. The at least one compound according to  claim 1 , wherein R 6  is an estolide residue. 
     
     
       8. The at least one compound according to  claim 1 , wherein v is an integer selected from 1 and 2. 
     
     
       9. The at least one compound according to  claim 5 , wherein W 2  is selected from 
       
         
           
           
               
               
           
         
       
     
     
       10. The at least one compound according to  claim 1 , wherein z is an integer selected from 2 to 8. 
     
     
       11. The at least one compound according to  claim 10 , wherein z is 6. 
     
     
       12. The at least one compound according to  claim 1 , wherein p is an integer selected from 1 to 5. 
     
     
       13. The at least one compound according to  claim 12 , wherein p is 1. 
     
     
       14. The at least one compound according to  claim 1 , wherein q is an integer selected from 1 to 8. 
     
     
       15. The at least one compound according to  claim 1 , wherein q is selected from 0 and 1. 
     
     
       16. The at least one compound according to  claim 1 , wherein q is an integer selected from 5 and 6. 
     
     
       17. The at least one compound according to  claim 1 , wherein W 2  is selected from —CHR 5 —, R 5  is selected from —S v R 6 , and p is an integer selected from 1 and 2. 
     
     
       18. The at least one compound according to  claim 17 , wherein v, independently for each occurrence, is an integer selected from 1 and 2. 
     
     
       19. The at least one compound according to  claim 1 , wherein W 2  is selected from 
       
         
           
           
               
               
           
         
       
       and p is 1. 
     
     
       20. The at least one compound according to  claim 1 , wherein the compound is selected from at least one compound according to Formula III: 
       
         
           
           
               
               
           
         
       
     
     
       21. The at least one compound according to  claim 1 , wherein n is an integer selected from 0 to 12. 
     
     
       22. The at least one compound according to  claim 21 , wherein n is an integer selected from 0 to 8. 
     
     
       23. The at least one compound according to  claim 22 , wherein n is an integer selected from 0 to 6. 
     
     
       24. The at least one compound according to  claim 1 , wherein n is equal to or greater than 1. 
     
     
       25. The at least one compound according to  claim 1 , wherein x+y is, independently for each chain, an integer selected from 13 to 19. 
     
     
       26. The at least one compound according to  claim 25 , wherein x+y is, independently for each chain, an integer selected from 13 to 15. 
     
     
       27. The at least one compound according to  claim 1 , wherein x+y is 15 for at least one chain. 
     
     
       28. The at least one compound according to  claim 1 , wherein R 2  is a branched or unbranched C 1  to C 20  alkyl that is saturated or unsaturated. 
     
     
       29. The at least one compound according to  claim 1 , wherein R 2  is selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, hexadecanyl, heptadecanyl, octadecanyl, nonadecanyl, and icosanyl, which are saturated or unsaturated and branched or unbranched. 
     
     
       30. The at least one compound according to  claim 28 , wherein R 2  is selected from C 6  to C 12  alkyl. 
     
     
       31. The at least one compound according to  claim 30 , wherein R 2  is 2-ethylhexyl. 
     
     
       32. The at least one compound according to  claim 1 , wherein R 2  is hydrogen. 
     
     
       33. The at least one compound according to  claim 1 , wherein R 2  is an unsubstituted alkyl that is saturated or unsaturated, and branched or unbranched. 
     
     
       34. The at least one compound according to  claim 20 , wherein z is 6 and q is an integer selected from 0 to 6.